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Raised in the Amish community of Harmony, Craig grew up with a limited knowledge of the outside world. Upon his 18th year, Craig partook in Rumspringa where he left the his community for a year and joined his brother, Greg, in the city of Los Santos to experience the wonders of city life.

After a year passed, Craig returned to a horror left behind by his father and decided to leave the Amish life behind forever.

Finding himself a storage container to live in and with his invention of the ratflail, Craig began his new life in the city of Los Santos.

Starting out as a salesman, Craig would stuff sandwiches, drinks, flashlights, and other odds and ends in his signature blue-striped jacket to sell to the populace while riding around on a blue bicycle. By going around selling these odds and ends, Craig eventually caught the attention of Jeffrey Connors whom then offered to have Craig work for as a game show host at Phoenix Corp. Until the game show was created, Craig would occasionally work as Security for Phoenix as well as a news anchor for Weazel news.

Craig's life was finally in motion from then on and he thought he had all that he could have ever asked for. He had a Job, a room in a hotel, electricity (which he immediately lost when microwaving a fork), and a new blue car. He had it all until one day he set eyes on what he thought was the most beautiful woman he had set eyes upon. Her name was Dolly Perkins, also known as the infamous DP. This dirt-smudged, blonde-haired, southern-accented, tobacco-stained, gator-skinned woman was accompanied by Clayton Colton, who then commenced to kidnap Craig along with his boss Lenny Moore. After an eventful day of mud-bathing and cow-tipping, Craig proposed to DP in the company of Jilly Hilljack's barber shop. Soon after DP was arrested for shooting Lenny, and was taken to jail. She was never seen again and Craig called off the engagement with a broken heart.

Life went on for Craig as Phoenix Corp started up a game show called Craig's Power Hour, with Craig as the host of the show. Craig grew in fame and popularity but felt more lonely than he ever had before. He would wander the streets of Los Santos in search of something to fill this void in his heart but never seemed to have any luck even after being rejected by almost every woman he came across.

One day while he was interviewing for Weazel News, Craig met another blonde-haired woman working at Big Boi Customs. She was oil-stained, southern-accented, and could have been mistaken for DP but was much more intelligent and fair. Craig had a thought "She looks like she could churn butter" and immediately asked her out for drinks. So started Craig's rocky, but sweet relationship with Darlene Pruitt.

After many adventures, both in the bedroom and out, Craig proposed to Darlene at the very place that the two had there first date up on the observatory overlooking Los Santos.

Around this time, something dark had begun to creep into Craig's consciousness and started to possess his thoughts with murder and distrust. This darkness provoked Craig into almost killing his good friend Cannon Rigs and admitted him into Parsons Rehabilitation Center.

After a week at Parsons Craig was released and officially diagnosed with paranoid schizophrenia.

On January 12th 2019, Craig and his fiance Darlene Pruitt were at the Luxury Motorsports with Tidus Martel, Lenny Moore, and a few others looking at cars. Craig and Darlene were having a conversation where Darlene says jokingly, "Just shoot me Craig, put me out of my fucking misery". Because of Craig's illness he takes this literally and pulls his firearm and shoots her point blank in the head. After she collapses, he realizes what he'd done and went catatonic whilst verbally repeating her name. Darlene sadly passed away the next day on January 13th, 2019.

Following the incident with Darlene at the car shop, Craig readmitted himself to Parsons. The day after he finds out about Darlene's death went into a state of distress, pacing the grounds of Parsons saying "I don't want to be here", while the voices inside his head taunted him calling him a murderer. He sent a 911 informing the San Andreas State Police that he was armed and dangerous. Commissioner McBride attempted to talk to him while Troopers Thomas and Armstrong provided over-watch. Upon the Commissioner's contact with Craig, he refused to put his gun down and started to shoot at McBride, which resulted in McBride and Thomas shooting him down. He was brought to the hospital where he was pronounced dead.